Tag: M.W=150-200

Ye, Bihai published the artcileRhodium-Catalyzed Asymmetric Conjugate Pyridylation with Pyridylboronic Acids, Quality Control of 371766-08-4, the publication is ACS Catalysis (2022), 12(4), 2434-2440, database is CAplus.

In this study, the rhodium-catalyzed asym. conjugate pyridylation of α,β-unsaturated carbonyl compounds with pyridylboronic acids was reported. The bifunctional chiral amide-diene ligand, which dramatically accelerated the reaction via possible H-bonding activation, and alc. solvent, which significantly inhibited the competing protodeboronation of pyridylboronic acids under rhodium catalysis, worked in concert to promote the reaction, thus enabling production of the pyridylation products in high yields (up to 99%) with good enantioselectivities (up to >99% ee).

ACS Catalysis published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C11H15NO2, Quality Control of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Zhou, Chao published the artcileMetal-Free, Redox-Neutral, Site-Selective Access to Heteroarylamine via Direct Radical-Radical Cross-Coupling Powered by Visible Light Photocatalysis, COA of Formula: C10H10N2, the publication is Journal of the American Chemical Society (2020), 142(39), 16805-16813, database is CAplus and MEDLINE.

Transition-metal-catalyzed C-N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chems. Reported herein is an alternative access to heteroarylamine via radical-radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C-N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C-N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.

Journal of the American Chemical Society published new progress about 46000-11-7. 46000-11-7 belongs to isoquinoline, auxiliary class Isoquinoline,Amine, name is N-Methylisoquinolin-1-amine, and the molecular formula is C18H28N2O7, COA of Formula: C10H10N2.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Solum, Eirik J. published the artcileSynthesis and biological evaluation of analogs of didehydroepiandrosterone as potential new anticancer agents, Category: isoquinoline, the publication is Molecules (2020), 25(13), 3052, database is CAplus and MEDLINE.

The synthesis, cytotoxicity and inhibition of CDK8 by thirteen analogs I (Ar = C₆H₅, isoquinolin-5-yl, indole-5-yl, etc.) of cortistatin A are reported. These efforts revealed that the analogs with either a 6- or 7-isoquinoline or 5-indole side chain in the 17-position are the most promising anti-proliferative agents. These compounds exhibited potent cytotoxic effects in CEM, HeLa and HMEC-1 cells. All three compounds exhibited IC₅₀ values < 10μM. The analog I (Ar = indole-5-yl) exhibited an IC50 value of 0.59μM towards the human dermal microvascular endothelial cell line (HMEC-1), significantly lower than the reference standard 2-methoxyestradiol. At a concentration at 50 nM the most potent I (Ar = isoquinolin-5-y) compound reduced the activity of CDK8 to 35%.

Molecules published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C22H18Cl2N2, Category: isoquinoline.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Gokanapalli, Anusha published the artcileInvestigation of Pd-PEPPSI catalysts and coupling partners towards direct C2-arylation/heteroarylation of benzoxazole, Synthetic Route of 371766-08-4, the publication is Applied Organometallic Chemistry (2021), 35(8), e6296, database is CAplus.

The motive of this current work was to conduct the direct C2-arylation reaction on benzoxazole with various cross-coupling partners like aryl/heteroaryl halide/carboxylic acid/diazonium tetrafluoroborate/sulfonyl chloride/boronic acids in the presence of different sym. and unsym. Pd-PEPPSI (pyridine-enhanced pre-catalyst preparation by stabilization initiation) catalysts via C (sp²)-C (sp²) bond formation. Compared with other coupling partners, boronic acids coupled with benzoxazole very efficiently in the presence of sterically and electronically tunable bulky 1,3-bis(N,N’-2,4,6-triisopropylbenzyl)benzimidazolium-Pd-PEPPSI complex in open air to offer the corresponding C2-aryl/heteroaryl benzoxazole compounds I [Ar = Ph, 4-MeC₆H₄, 3-thienyl, etc.]. Further, it was worthy to mention that there was no need of any external oxidant/ligand/additive for the complete conversion of starting mols. to products. The reactions progressed successfully with a wide range of substrate scope and attained the products in good to excellent yields in a short reaction time in ethanol/water (1:1) medium. Greatly, catalysts could be recovered and reused for few cycles with significant reactivity.

Applied Organometallic Chemistry published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Synthetic Route of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Yamaoka, Nagahisa published the artcileIdentification of novel plasminogen activator inhibitor-1 inhibitors with improved oral bioavailability: Structure optimization of N-acylanthranilic acid derivatives, Formula: C9H8BNO2, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(4), 809-813, database is CAplus and MEDLINE.

Novel plasminogen activator inhibitor-1 (PAI-1) inhibitors with highly improved oral bioavailability were discovered by structure-activity relationship studies on N-acyl-5-chloroanthranilic acid derivatives Because lipophilic N-acyl groups seemed to be important for the anthranilic acid derivatives to strongly inhibit PAI-1, synthesis of compounds in which 5-chloroanthranilic acid was bound to a variety of highly lipophilic moieties with appropriate linkers was investigated. As the result it appeared that some of the derivatives possessing aryl- or heteroaryl-substituted Ph groups in the acyl chain had potent in vitro PAI-1 inhibitory activity. Oral absorbability of typical compounds was also evaluated in rats, and three compounds which have diverse chem. structure with each other, e.g., I, were selected for further pharmacol. evaluation.

Bioorganic & Medicinal Chemistry Letters published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H5FO2, Formula: C9H8BNO2.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Chen, Yiding published the artcileDirect Copper-Catalyzed Three-Component Synthesis of Sulfonamides, Quality Control of 371766-08-4, the publication is Journal of the American Chemical Society (2018), 140(28), 8781-8787, database is CAplus and MEDLINE.

Sulfonamides such as N-(phenylsulfonyl)morpholine were prepared in one step by coupling of aryl-, heteroaryl-, and alkenylboronic acids such as phenylboronic acid with cyclic and acyclic alkyl secondary amines such as morpholine and primary anilines and the bis(sulfur dioxide) complex of DABCO (DABSO) in the presence of Cu(OTf)₂ and 4,4′-dimethoxy-2,2′-bipyridine in DMSO. The method was used on gram scale and was used to prepare sulfonamides from drugs and drug fragments.

Journal of the American Chemical Society published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Quality Control of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Cheng, Yunfeng published the artcileA New Class of Fluorescent Boronic Acids That Have Extraordinarily High Affinities for Diols in Aqueous Solution at Physiological pH, Application In Synthesis of 371766-08-4, the publication is Chemistry – A European Journal (2010), 16(45), 13528-13538, S13528/1-S13528/40, database is CAplus and MEDLINE.

The boronic acid group is an important recognition moiety for sensor design. Herein, the authors report a series of isoquinolinylboronic acids that have extraordinarily high affinities for diol-containing compounds at physiol. pH. In addition, 5- and 8-isoquinolinylboronic acids also showed fairly high binding affinities towards D-glucose (K_a=42 and 46 M^-1, resp.). For the first time, weak but encouraging binding of cis-cyclohexanediol was found for these boronic acids. Such binding was coupled with significant fluorescence changes. Furthermore, 4- and 6-isoquinolinylboronic acids also showed the ability to complex Me α-D-glucopyranose (K_a=3 and 2 M^-1, resp.).

Chemistry – A European Journal published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Application In Synthesis of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Duncton, Matthew A. J. published the artcileArylphthalazines as potent, and orally bioavailable inhibitors of VEGFR-2, Computed Properties of 371766-08-4, the publication is Bioorganic & Medicinal Chemistry (2009), 17(2), 731-740, database is CAplus and MEDLINE.

A series of arylphthalazine derivatives were synthesized and evaluated as antagonists of VEGF receptor II (VEGFR-2). IM-094482 57, which was prepared in two steps from com. available starting materials, was found to be a potent inhibitor of VEGFR-2 in enzymic, cellular and mitogenic assays (comparable activity to ZD-6474). Addnl., 57 inhibited the related receptor, VEGF receptor I (VEGFR-1), and showed excellent exposure when dosed orally to female CD-1 mice.

Bioorganic & Medicinal Chemistry published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Computed Properties of 371766-08-4.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Duncton, Matthew A. J. published the artcileArylphthalazines. Part 2: 1-(Isoquinolin-5-yl)-4-arylamino phthalazines as potent inhibitors of VEGF receptors I and II, Recommanded Product: Isoquinolin-5-ylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(6), 1579-1581, database is CAplus and MEDLINE.

A novel class of 1-(isoquinolin-5-yl)-4-arylamino-phthalazines is described as inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). Many compounds display VEGFR-2 inhibitory activity with an IC₅₀ as low as 0.017 μM in an HTRF enzymic assay. The compounds also inhibit VEGFR-1, a related tyrosine kinase.

Bioorganic & Medicinal Chemistry Letters published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Recommanded Product: Isoquinolin-5-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem

Li, Shasha published the artcileMerging Late-Stage Diversification with Solid-Phase Peptide Synthesis Enabled by High-Throughput On-Resin Reaction Screening, Recommanded Product: Isoquinolin-5-ylboronic acid, the publication is ACS Catalysis (2022), 12(5), 3201-3210, database is CAplus.

An integrated workflow is described that combines micromole-scale high-throughput experimentation (HTE) reaction screening and solid-phase peptide synthesis (SPPS) to enable rapid synthetic method development for on-resin peptide diversification. Using this new approach, we have identified several sets of robust Suzuki-Miyaura coupling conditions with complementary scope that collectively display broad coverage with respect to both resin-bound peptide substrates containing aryl halide side chains and (hetero)arylboronic acid coupling partners. We have also demonstrated the utility of this integrated SPPS/chem. diversification method by synthesizing a multidimensional library of diverse peptides in high yields.

ACS Catalysis published new progress about 371766-08-4. 371766-08-4 belongs to isoquinoline, auxiliary class Isoquinoline,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is Isoquinolin-5-ylboronic acid, and the molecular formula is C9H8BNO2, Recommanded Product: Isoquinolin-5-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Isoquinoline,
Isoquinoline | C9H7N – PubChem